1. You've Got Mail (opens in new tab)
If there's one thing guaranteed to please a crowd, it's a Tom Hanks and Meg Ryan romance. The classic tale of mistaken identity (and, oddly enough, the ins and outs of corporate book-selling) is charming enough that its take on the Internet — chat rooms, for goodness sakes — doesn't even seem dated, it just seems adorable. Set during the holiday season, it earns bonus points for cheer.
2. Good Will Hunting (opens in new tab)
It's probably been way too long since anyone in your family sat down to watch the feature that put Matt Damon and Ben Affleck on the map, so why not rectify that together? Good Will Hunting even includes one of dearly departed Robin Williams's finest performances, in addition to wit and heart in equal measure.
3. Cutie and the Boxer (opens in new tab)
The Oscar-nominated documentary might sound too cerebral for holiday consumption – it's about the tumultuous relationship between an artist and his wife – but the final product is touching, funny, and relatable.
4. Catching Fire (opens in new tab)
You obviously need to need to watch (or rewatch) this before piling into the car and driving to the movie theater to see Mockingjay - Part 1.
5. The Queen of Versailles (opens in new tab)
This award-winning Sundance documentary will effectively cure any desire for your family to overspend on Black Friday (it's about one of America's richest families and their major money troubles) while also providing a screamingly funny inside look at a wacky decadent lifestyle typically seen only on reality television.
6. Silver Linings Playbook (opens in new tab)
Everyone loves Jennifer Lawrence. And Bradley Cooper. And Robert De Niro. And dancing.
7. Joan Rivers: A Piece of Work (opens in new tab)
We've lost a lot of wonderful people this year, and the divinely acid-tongued Ms. Rivers is one of them. Even if you've never been particularly endeared to the comedian, this insightful and wildly funny documentary will change that.
8. Skyfall (opens in new tab)
James Bond is always a crowd-pleaser, and the latest entry into the ever-expanding 007 canon offers up both action and drama to spare.
9. 20 Feet From Stardom (opens in new tab)
This year's Oscar winner for Best Documentary is a full cinematic experience, and one that just so happens to sound damn good as it goes down. The feature chronicles some of music's most underappreciated talents (back-up singers), and weaves in inspiring stories with some incredible music. Your entire family will be dancing in no time.
10. In A World … (opens in new tab)
The amazingly talented Lake Bell wrote, directed, and starred in this hilarious 2013 comedy about the weird world of movie voiceover artists. Despite its highly-specific subject matter, the film still works as an uproarious story about a gal just trying to make it. Even better? Her dad just happens to be the world's best voiceover guy, so it's got extra family resonance.
11. The Muppet Christmas Carol (opens in new tab)
Get in the holiday spirit with everyone's favorite fuzzy puppets as they put their own spin on Dickens' classic tale.
12. Frances Ha (opens in new tab)
Do your parents not quite understand your current lifestyle choices? Introduce them to the incredibly charming (and slightly dunderheaded) Frances Ha. Odds are, they'll feel much better about your direction in life, even as they fall totally in love with the perfect creature that is Greta Gerwig.
13. Sleepless in Seattle (opens in new tab)
There's no better way to follow up You've Got Mail than with yet another Hanks/Ryan pairing. Get out the hankies.
14. The Parent Trap (opens in new tab)
Sure, the Hayley Mills original is a classic, but this modern take on the old "separated at birth" story is funnier and flashier. It also features Lindsay Lohan in her most adorable role ever, which may make for some awkward conversation when your grandmother inevitably asks you, "what's that cute girl up to these days?"
15. Cool Runnings (opens in new tab)
It's an inspirational sports tale that feels appropriate for the season without actually compelling anyone to take up a new sport during their holiday break!
16.Annie (opens in new tab)
We're getting a brand new Annie movie this Christmas, so now is the perfect time to catch upon hard knock lives, fluffy puppies, and enough good cheer to make the entire family stand up and sing.
17. Roman Holiday (opens in new tab)
Holiday break is a wonderful time to catch up on classic features that might have otherwise eluded you, including the kind of stuff that will send your grandparents swooning into their own memories of Audrey Hepburn, Gregory Peck, and the Italy of yesteryear.
18. Swiss Family Robinson (opens in new tab)
The ultimate family bonding feature.
19. Honey, I Shrunk the Kids (opens in new tab)
The ultimate tiny family bonding feature.
20. Scrooged (opens in new tab)
Still need to un-grump-ify a family member? Tease them witha Bill Murray comedy that packs a cheerful holiday punch, complete with ribaldjokes, a classic tale, and a satisfying end that guarantees lots of familyhugs.
Via Cosmo (opens in new tab)
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